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77956069256
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General review on aza-MBH reactions and their applications
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General review on aza-MBH reactions and their applications
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2
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59649098742
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Declerck, V., Martinez, J., and Lamaty, F. Chem. Rev. 2009, 109, 1
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Chem. Rev.
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Declerck, V.1
Martinez, J.2
Lamaty, F.3
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3
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77956087105
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Reviews on catalytic enantioselective aza-MBH reactions
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Reviews on catalytic enantioselective aza-MBH reactions
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4
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34347262098
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Masson, G., Housseman, C., and Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 4614
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Masson, G.1
Housseman, C.2
Zhu, J.3
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0037011306
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Shi, M. and Xu, Y.-M. Angew. Chem., Int. Ed. 2002, 41, 4507
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Shi, M.1
Xu, Y.-M.2
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Shi, M., Xu, Y.-M., and Shi, Y.-L. Chem. - Eur. J. 2005, 11, 1794
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Shi, M.1
Xu, Y.-M.2
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Shi, M., Chen, L.-H., and Li, C.-Q. J. Am. Chem. Soc. 2005, 127, 3790
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Shi, M.1
Chen, L.-H.2
Li, C.-Q.3
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33744818862
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Liu, Y.-H., Chen, L.-H., and Shi, M. Adv. Synth. Catal. 2006, 348, 973
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Liu, Y.-H.1
Chen, L.-H.2
Shi, M.3
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50649095554
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Guan, X.-Y., Jiang, Y.-Q., and Shi, M. Eur. J. Org. Chem. 2008, 2150
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Eur. J. Org. Chem.
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Guan, X.-Y.1
Jiang, Y.-Q.2
Shi, M.3
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37649015237
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See also ref 2b
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Qi, M.-J., Ai, T., Shi, M., and Li, G. Tetrahedron 2008, 64, 1181 See also ref 2b.
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(2008)
Tetrahedron
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Qi, M.-J.1
Ai, T.2
Shi, M.3
Li, G.4
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13
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15744396095
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Matsui, K., Takizawa, S., and Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680
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(2005)
J. Am. Chem. Soc.
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Matsui, K.1
Takizawa, S.2
Sasai, H.3
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33645395732
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Matsui, K., Takizawa, S., and Sasai, H. Synlett 2006, 761
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Synlett
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Matsui, K.1
Takizawa, S.2
Sasai, H.3
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For selected recent examples, see
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For selected recent examples, see: Abermil, N., Masson, G., and Zhu, J. Org. Lett. 2009, 11, 4648
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(2009)
Org. Lett.
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, pp. 4648
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Abermil, N.1
Masson, G.2
Zhu, J.3
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17
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33746298422
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For other examples, see refs 1 and 2
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Gausepohl, R., Buskens, P., Kleinen, J., Bruckmann, A., Lehmann, C. W., Klankermayer, J., and Leitner, W. Angew. Chem., Int. Ed. 2006, 45, 3689 For other examples, see refs 1 and 2.
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(2006)
Angew. Chem., Int. Ed.
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Gausepohl, R.1
Buskens, P.2
Kleinen, J.3
Bruckmann, A.4
Lehmann, C.W.5
Klankermayer, J.6
Leitner, W.7
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Abermil, N., Masson, G., and Zhu, J. J. Am. Chem. Soc. 2008, 130, 12596
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(2008)
J. Am. Chem. Soc.
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Abermil, N.1
Masson, G.2
Zhu, J.3
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77949860742
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Abermil, N., Masson, G., and Zhu, J. Adv. Synth. Catal. 2010, 352, 656
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(2010)
Adv. Synth. Catal.
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Abermil, N.1
Masson, G.2
Zhu, J.3
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77956082180
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For partially successful early trials using acrylates, see ref 3a, 3c. See also
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For partially successful early trials using acrylates, see ref 3a, 3c. See also
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23
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0141743697
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Kawahara, S., Nakano, A., Esumi, T., Iwabuchi, Y., and Hatakeyama, S. Org. Lett. 2003, 5, 3103
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(2003)
Org. Lett.
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Kawahara, S.1
Nakano, A.2
Esumi, T.3
Iwabuchi, Y.4
Hatakeyama, S.5
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24
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77956091687
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3/linked-BINOL 1a complex as a Lewis acid/Brønsted base bifunctional catalyst for asymmetric Michael reaction of malonates
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3/linked-BINOL 1a complex as a Lewis acid/Brønsted base bifunctional catalyst for asymmetric Michael reaction of malonates
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25
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0001392528
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Kim, Y. S., Matsunaga, S., Das, J., Sekine, A., Ohshima, T., and Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506
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Kim, Y.S.1
Matsunaga, S.2
Das, J.3
Sekine, A.4
Ohshima, T.5
Shibasaki, M.6
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0037189163
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Takita, R., Ohshima, T., and Shibasaki, M. Tetrahedron Lett. 2002, 43, 4661
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(2002)
Tetrahedron Lett.
, vol.43
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Takita, R.1
Ohshima, T.2
Shibasaki, M.3
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77956088776
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For synthesis of linked-BINOLs, see 1a
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For synthesis of linked-BINOLs, see 1a
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0034654056
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1b:, Angew. Chem., Int. Ed. 2005, 44, 4365
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Matsunaga, S., Das, J., Roels, J., Vogl, E. M., Yamamoto, N., Iida, T., Yamaguchi, K., and Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. 1b: Harada, S., Handa, S., Matsunaga, S., and Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 4365
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Matsunaga, S.1
Das, J.2
Roels, J.3
Vogl, E.M.4
Yamamoto, N.5
Iida, T.6
Yamaguchi, K.7
Shibasaki, M.8
Harada, S.9
Handa, S.10
Matsunaga, S.11
Shibasaki, M.12
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28244460830
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Sugita, M., Yamaguchi, A., Yamagiwa, N., Handa, S., Matsunaga, S., and Shibasaki, M. Org. Lett. 2005, 7, 5339
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(2005)
Org. Lett.
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Sugita, M.1
Yamaguchi, A.2
Yamagiwa, N.3
Handa, S.4
Matsunaga, S.5
Shibasaki, M.6
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77956093993
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3 complex with DABCO was reported as an efficient system for the reaction of aldehydes with acrylates
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3 complex with DABCO was reported as an efficient system for the reaction of aldehydes with acrylates.
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31
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Yang, K.-S., Lee, W.-D., Pan, J.-F., and Chen, K. J. Org. Chem. 2003, 68, 915
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J. Org. Chem.
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Yang, K.-S.1
Lee, W.-D.2
Pan, J.-F.3
Chen, K.4
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5344224096
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For reviews on acid/base bifunctional asymmetric catalysis, see
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For reviews on acid/base bifunctional asymmetric catalysis, see: Ma, J.-A. and Cahard, D. Angew. Chem., Int. Ed. 2004, 43, 4566
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(2004)
Angew. Chem., Int. Ed.
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Cahard, D.2
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Yamamoto, H. and Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924
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Angew. Chem., Int. Ed.
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Yamamoto, H.1
Futatsugi, K.2
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Taylor, M. S. and Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520
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Taylor, M.S.1
Jacobsen, E.N.2
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Mukherjee, S., Yang, J. W., Hoffmann, S., and List, B. Chem. Rev. 2007, 107, 5471
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Mukherjee, S.1
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Shibasaki, M., Kanai, M., Matsunaga, S., and Kumagai, N. Acc. Chem. Res. 2009, 42, 1117
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Acc. Chem. Res.
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Shibasaki, M.1
Kanai, M.2
Matsunaga, S.3
Kumagai, N.4
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77956067793
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Initial screening with other BINOL derivatives resulted in poor enantioselectivity
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Initial screening with other BINOL derivatives resulted in poor enantioselectivity.
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37849014325
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For positive effects of achiral Brønsted acids to accelerate catalytic asymmetric aza-MBH reaction, see refs 3e, 5a, and 7. The effects of the proton source in Morita-Baylis-Hillman reactions of aldehydes were investigated in detail; see:, and references therein
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For positive effects of achiral Brønsted acids to accelerate catalytic asymmetric aza-MBH reaction, see refs 3e, 5a, and 7. The effects of the proton source in Morita-Baylis-Hillman reactions of aldehydes were investigated in detail; see: Robiette, R., Aggarwal, V. K., and Harvey, J. N. J. Am. Chem. Soc. 2007, 129, 15513 and references therein
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J. Am. Chem. Soc.
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Robiette, R.1
Aggarwal, V.K.2
Harvey, J.N.3
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2,6-Di- t Bu-phenol, 2,6-di- t Bu-4-MeO-phenol, 2- t Bu-phenol, and 2- t Bu-4-MeO-phenol also had positive effects, and 4a was obtained in greater than 80% yield and 87-89% ee. 4,4′-Thiobis(6- t- Bu- m -cresol) was selected for further studies, because it gave the highest enantioselectivity
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2,6-Di- t Bu-phenol, 2,6-di- t Bu-4-MeO-phenol, 2- t Bu-phenol, and 2- t Bu-4-MeO-phenol also had positive effects, and 4a was obtained in greater than 80% yield and 87-89% ee. 4,4′-Thiobis(6- t- Bu- m -cresol) was selected for further studies, because it gave the highest enantioselectivity.
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For the utility of 4,4′-thiobis(6- t- Bu- m -cresol) as a radical inhibitor in organic synthesis, see
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For the utility of 4,4′-thiobis(6- t- Bu- m -cresol) as a radical inhibitor in organic synthesis, see
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For the utility as an antioxidant for stabilizing polymers, see: Polym. Eng. Sci. 1966, 231
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Kishi, Y., Aratani, M., Tanino, H., Fukuyama, T., Goto, T., Inoue, S., Sugiura, S., and Kakoi, H. J. Chem. Soc., Chem. Commun. 1972, 64 For the utility as an antioxidant for stabilizing polymers, see: Gordon, D. A. and Rothstein, E. C. Polym. Eng. Sci. 1966, 6, 231
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(1972)
J. Chem. Soc., Chem. Commun.
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Kishi, Y.1
Aratani, M.2
Tanino, H.3
Fukuyama, T.4
Goto, T.5
Inoue, S.6
Sugiura, S.7
Kakoi, H.8
Gordon, D.A.9
Rothstein, E.C.10
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Aggarwal, V. K., Emme, I., and Fulford, S. Y. J. Org. Chem. 2003, 68, 692
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J. Org. Chem.
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Aggarwal, V.K.1
Emme, I.2
Fulford, S.Y.3
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The absolute configuration of 4a was determined by comparing the sign of the optical rotation with the reported data reported in ref 8b
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The absolute configuration of 4a was determined by comparing the sign of the optical rotation with the reported data reported in ref 8b.
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85% deuterated 3 was used for the experiments depicted in Figure 2. The degree of deuteration of 3 did not change under the reaction conditions in Figure 2 as confirmed by NMR
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85% deuterated 3 was used for the experiments depicted in Figure 2. The degree of deuteration of 3 did not change under the reaction conditions in Figure 2 as confirmed by NMR.
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See Supporting Information for experimental data
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See Supporting Information for experimental data.
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Possibility of the enantio-differentiation at the proton transfer step, which is often postulated in other systems (see ref 6), cannot be excluded. But, we speculate that the enantioselectivity would be kinetically determined at the C-C bond-formation step, because the proton transfer step is fast in the present system
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Possibility of the enantio-differentiation at the proton transfer step, which is often postulated in other systems (see ref 6), cannot be excluded. But, we speculate that the enantioselectivity would be kinetically determined at the C-C bond-formation step, because the proton transfer step is fast in the present system.
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